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Cannabis As a Plant: Taxonomy and Chemistry (PDF) Cannabis as a plant: Taxonomy and Chemistry Monique McHenry, Ph.D. Assistant Professor of Pharmacology, University of Vermont Co-founder, CASE Institute Disclaimer & Disclosure • I am a member of the faculty at the University of Vermont • Materials presented here represent my own findings, views and opinions and should not be taken as a statement, position, opinion, or endorsement by the University of Vermont University of Vermont Health Network Discussion includes investigational drugs not approved for use in the United States. DISCLOSURE: Is there anything to disclose? Yes Please list the Potential Conflict of Interest (if applicable): Relationships with Vermont Patients Alliance and Phytoscience Institute All Potential Conflicts of Interest have been resolved prior to the start of this program. Yes (If no, credit will not be awarded for this activity.) All recommendations involving clinical medicine made during this talk were based on evidence that is accepted within the profession of medicine as adequate justification for their indications and contraindications in the care of patients. Yes Cannabis history Human use 12,000-10,000 years ago Cannabis cultivation begins 1753 Linnaeus classifies Cannabis sativa L. 2011 First Cannabis genome is sequenced Policy 1930 Harry Anslinger began the process of criminalization and prohibition of drugs including marijuana and by 1931 29 states had outlawed Cannabis. 1970 Controlled Substances Act passed. Cannabis is Schedule one drug categorized to have a high potential for abuse and no medicinal value. 1996 Passage of the Compassionate Use Act initiative Medical discovery 1964 Tetrahydrocannabinol (THC) is isolated and synthesized 1988 Cannabinoid receptors CB1 and CB2 discovered 1992 Endogenous cannabinoids discovered 3 Cannabis history Hemp is removed from CSA 10,000 BCE - 0 Used as a Gains popularity as a Criminalized therapeutic drug therapeutic drug Cannabis history Source: By Lokal_Profil, CC BY-SA 2.5, https://commons.wikimedia.org/w/index.php?curid=2370050 Cannabis history • The ancestral distribution of Cannabis is central Asia (Li, 1974) • Cannabis arrived in the Americas after 1545 (Small et al., 1975) • Currently Cannabis is distributed world-wide Photo credits: Hillig and Mahlberg, 2004; Angiosperm Phylogeny Group, 2015 Cannabis plant biology Macroscopic morphological characters – Leaves, flowers, and fruit Photo credit: http://en.wikipedia.org/wiki/Cannabis Cannabis plant biology Microscopic morphological characters - Trichomes and glands Cannabis plant biology Reproductive characters – Male and female flowers are found on different plants Female flower Male flower – Wind Pollinated Pollen Photo credit: http://plant.pictures.com; http://www.internationalhempassociation.org/jiha/jiha5208.html Cannabis plant biology Plants produce chemical compounds, phytochemicals, as part of their normal metabolic activities. Phytochemicals are divided into two groups: 1. Primary metabolites • found in all plants, serve basic plant functions • i.e. sugars and fats 2. Secondary metabolites • found in select plants, serve in a Wounded poppy Morphine, the more specific function fruit exuding opium active principle of • i.e. opium, phytocannabinoids opium Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis plant biology Plants produce chemical compounds, phytochemicals, as part of their normal metabolic activities. Phytochemicals are divided into two groups: 1. Primary metabolites • found in all plants, serve basic plant functions • i.e. sugars and fats 2. Secondary metabolites Cannabis glandular Delta-9- • found in select plants, serve in a trichomes containing tetrahydrocannabinol, more specific function phytocannabinoids one active principle of • i.e. opium, phytocannabinoids Cannabis Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis chemicals Slide content contributed by Dr. Wolfgang Dostmann, UVM COM; source Potter, 2009 Cannabis chemicals The main biologically active phytocannabinoids Delta-9-tetrahydrocannabinol (THC) • Partial Agonist CB1/CB2 receptors • Psychoactive • Anti-pain, anti-nausea • Anti-spasm, anti-immune Cannabidiol (CBD) • Antagonist CB1/CB2 receptors • Not psychoactive • Anti-seizure activity Activated by heating the plant Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis chemicals What are Phytocannabinoids? Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis chemicals How are Phytocannabinoids manufactured by the plant? Phytocannabinoid biosynthesis 1. Chemical precursors are absorbed through the roots from the soil 2. CBD & THC derive from CBG compounds, catalyzed by the enzyme THCA synthase or CBDA synthase • CBDA synthase is dominant • Hemp has THCA & CBA synthase • Drug-type (Marijuana) has THCA & CBDA synthase • nonfunctional CBDA synthase Source: Weilben et al., 2015 Cannabis chemicals Phytocannabinoids evolved in Cannabis Herbivory defense? Environmental response? Cannabis chemicals Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis chemicals What are the non-cannabinoids? Terpenes (Myrcene) Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis chemicals Myrcene has an analgesic effect “Terpenes such as myrcene may constitute a lead for the development of new peripheral analgesics with a profile of action different from that of the aspirin-like drugs.” Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis chemicals α-Pinene appears to be a broad-spectrum antibiotic •Does α-Pinene in three hemp cultivars have an inhibitory activity of microbial growth? •Yes, results demonstrate α-Pinene (in hemp essential oils) significantly inhibits microbial growth • Gram (+ and -) bacteria • Yeasts •Conclusion: industrial hemp essential oils applications could control spoilage, food-borne pathogens, and phytopathogen microorganisms. Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis chemicals Boiling point Partition Coefficient, logP Myrcene 166 °C (330 °F) 4.30 Limonene 176 °C (349 °F) 3.40 Linalool 198 °C (388 °F) 2.65 α-Pinene 155 °C (311 °F) 2.80 Geraniol 230 °C (446 °F) 3.28 THC 157 °C (315 °F) 6.97 CBD 180 °C (356 °F) 6.33 CBN 185 °C (365 °F) 6.93 Slide content contributed by Dr. Wolfgang Dostmann, UVM LCOM Cannabis chemicals Why does Cannabis produce Phytocannabinoids? Level of Phytocannabinoids Cannabis chemicals Why does Cannabis produce Phytocannabinoids? What we know…. Plant organ matters! Highest amount of THC & CBD is found in flower (Andre et al., 2016) Cannabis chemicals Why does Cannabis produce Phytocannabinoids? What we know…. Size matters! The amount of THC is correlated to the size of resin gland (Small and Naraine, 2015) Cannabis chemicals Why does Cannabis produce Phytocannabinoids? What we know…. Light quality matters! •Magagnini et al. (2018) Phytocannabinoid yield changes with different light sources –Perhaps complex mechanisms mediated by the UV-A and blue wavelengths that induce CBG accumulation (CBG is precursor of other phytocannabinoids) g flower/plant % THC % CBD • Lydon et al. (1987) In “drug-type” plants, increasing levels of UV-B Cannabinoid/g radiation corresponded with increased levels of THC –Potential for selective pressure to favor “drug-type” plants in environments with high levels of UV radiation Cannabis chemicals Why does Cannabis produce Phytocannabinoids? Desiccation Prevention? •Major Phytocannabinoids increased when intentional drought applied seven weeks into reproductive stage (Caplan, 2018) Caplan, 2018 Hot and Cool and •Wild plants in cool humid environments dry humid had fewer glandular hair compared to plants in hot dry environments (Sharma, 1975) •Higher THC levels measured in drier continental climate compared to maritime climate (Murari et al., 1983) Sharma, 1975 Cannabis chemicals Why does Cannabis produce Phytocannabinoids? Stress? • Correlation between low plant height and high Phytocannabinoid content • Low Mg, higher THC & CBD content (Coffman and Gentner, 1975) Cannabis chemicals Why does Cannabis produce Phytocannabinoids? Insecticide? • THC-rich Mexican (vs. CBD-rich Turkish) Cannabis was reported fatal to tiger moth (Arctia caja) larvae (Rothschild et al., 1977) Cannabis chemicals Why does Cannabis produce Phytocannabinoids? Chemical plant defense? • Cannabis extract inhibited germination of Lettuce (Lactuca sativa) (Mahmoodzadeh et al., 2015) • Cannabis extract decreased the germination of monocots (Pedulko, 2014) Cannabis chemicals Why does Cannabis produce Phytocannabinoids? Disease prevention? – Harbor antibiotic properties (ElSohly et al. 1982) – Antibiotic properties assist in the overwintering of seed (Ferency, 1956) Cannabis chemicals Why are the amounts of Phytocannabinoids inconsistent? Plant age changes Phytocannabinoid content • THC increases throughout the life cycle of Cannabis before reaching a plateau (De backer et al., 2012) https://www.cannabisreports.com/news/2016/03/07/study-examines- cannabinoid-terpene-development-patterns-three-cannabis- chemotypes/ Cannabis chemicals Why are the amounts of Phytocannabinoids inconsistent? Phytocannabinoid difference due to changes in: • Genetics • Plant Organ • Light • Soil composition • Available moisture • Age Aizpurua-Olaizola et al., 2016 Cannabis chemicals Is it possible to grow Cannabis with reproducible terpene and Phytocannabinoid levels? • Yes! As long as environmental conditions and genetics are standardized – Fischedick et al. (2010) • 11 “strains” • 36 compounds • Control for grow cycle time,
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